Can't offer any words of wisdom, in fact you've only confirmed we have the same problem way back on 2.1 (15). We thought it was intermittent problems on external call transfer but it is actually all IPO initiated calls.
You need software version 2.1 (31) or higher or 3.0 or 3.1
Then you have the tickbox.
So upgrade to 2.1(51) and tick allow outgoing transfer in the systemtab/telefony.
You don't want to make changes with an admin software that does not match the correct ver of firmware on the system. If you do, you run the risk of corupting the file and having to reset your system using the serial port on the back.
So in short, upgrade the firmware if you're wanting to make this change.
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